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$208+ Cheap flights from Midland (MAF) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — SJU
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Cheap flight deals from Midland to Caribbean

Keep the following information in mind while searching for Midland to Caribbean flight deals. Data was last updated October 14, 2025.

Round-trip from

$362
(United Airlines)

One-way from

$208
(Southwest)

Popular in

July

Cheapest in

April

Average price

$582
From Midland Intl to Caribbean
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One-way flight from Midland Intl to Caribbean
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Highest demand for flights based on searches. 3% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Midland to Caribbean

Cheapest flights from Midland to Caribbean
Explore the most affordable flight options available from Midland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/297:56 amMAF - SJU
2 stops11h 04mUnited Airlines
Wed 11/53:46 pmSJU - MAF
1 stop7h 56mUnited Airlines
Deal found 10/14$362
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2910:45 amMAF - SJU
2 stops12h 05mSouthwest
Wed 11/52:05 pmSJU - MAF
2 stops10h 05mSouthwest
Deal found 10/14$402
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/305:00 amMAF - SJU
2 stops12h 10mAmerican Airlines
Thu 11/67:15 amSJU - MAF
1 stop18h 40mAmerican Airlines
Deal found 10/14$422
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/311:00 amMAF - SJU
2 stops8h 30mSouthwest
Mon 11/172:05 pmSJU - MAF
2 stops10h 05mSouthwest
Deal found 10/14$515
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/265:30 amMAF - SJU
2 stops10h 15mSouthwest
Sun 11/25:40 amSJU - MAF
2 stops12h 30mSouthwest
Deal found 10/14$519
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/307:00 amMAF - SJU
1 stop7h 36mUnited Airlines
Wed 11/52:05 amSJU - MAF
2 stops13h 52mUnited Airlines
Deal found 10/14$525
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:00 amMAF - SJU
1 stop7h 36mUnited Airlines
Sat 11/12:05 amSJU - MAF
2 stops12h 40mUnited Airlines
Deal found 10/14$622
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/39:13 amMAF - SJU
2 stops12h 45mAmerican Airlines
Mon 11/177:15 amSJU - MAF
1 stop8h 43mAmerican Airlines
Deal found 10/14$655
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/265:00 amMAF - SJU
1 stop8h 20mAmerican Airlines
Sun 11/23:56 pmSJU - MAF
1 stop8h 42mAmerican Airlines
Deal found 10/14$780

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 14, 2025.
Use the filters below to find and compare flights from Midland to Caribbean that are best for you.

Fly from

Midland

Fly to

Caribbean

Route

Depart

Return

Price

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 10/29

6:00 am-2:25 pm

1 stop7h 25m

San Juan Luis Munoz Marin Intl

Wed 11/5

7:15 am-10:53 pm

1 stop17h 38m

$362

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 10/29

7:56 am-8:00 pm

2 stops11h 04m

San Juan Luis Munoz Marin Intl

Wed 11/5

3:46 pm-9:42 pm

1 stop7h 56m

$362

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 3/10

9:35 am-8:26 pm

1 stop9h 51m

San Juan Luis Munoz Marin Intl

Wed 3/11

7:10 am-6:20 pm

2 stops12h 10m

$364

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Wed 10/29

10:45 am-11:50 pm

2 stops12h 05m

San Juan Luis Munoz Marin Intl

Wed 11/5

2:05 pm-10:10 pm

2 stops10h 05m

$402

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Thu 10/30

5:45 am-7:25 pm

2 stops12h 40m

San Juan Luis Munoz Marin Intl

Thu 11/6

6:40 am-4:30 pm

2 stops11h 50m

$402

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sun 2/1

7:20 am-6:25 pm

1 stop9h 05m

San Juan Luis Munoz Marin Intl

Sun 2/8

7:45 am-4:21 pm

1 stop10h 36m

$413

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Tue 3/10

5:00 am-1:05 pm

1 stop8h 05m

Montego Bay Sangster Intl

Wed 3/11

2:20 pm-11:30 pm

1 stop9h 10m

$651

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Tue 3/10

8:02 am-1:44 pm

1 stop5h 42m

Montego Bay Sangster Intl

Wed 3/11

5:00 pm-10:28 pm

2 stops29h 28m

$656

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

Mon 4/6

4:55 pm-11:55 am

2 stops18h 00m

Santo Domingo Las Americas

Wed 4/8

1:10 pm-8:45 am

2 stops20h 35m

$672

MidlandSimpson Bay

MAF - SXM

MAFSXM

Midland Intl

Mon 4/6

6:43 pm-3:15 pm

2 stops19h 32m

Simpson Bay Princess Juliana

Thu 4/9

2:35 pm-8:49 am

2 stops19h 14m

$720

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/13

Showing 1-10 of 16 results
1
2

Best time to book a flight from Midland to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Midland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Midland to Caribbean

What is the cheapest month to book a flight from Midland to Caribbean?

Currently, April is the cheapest month in which you can book a flight from Midland to Caribbean (average of $247). Flying from Midland to Caribbean in July is currently the most expensive (average of $666). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MAF to CB?

Find hourly flight availability from Midland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 14, 2025.

It’s typically best to fly out from Midland to Caribbean in the evening. Doing so could potentially save you 23% on the flight price compared to flying at noon, which is usually more expensive.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated October 14, 2025.
Read through reviews of airlines operating flights from Midland to Caribbean, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,976 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,042 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midland to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Midland to Caribbean?

    Most people fly from Midland Intl (MAF) if they book a flight from Midland to Caribbean. Midland Intl is conveniently located just 8.2 mi from Midland’s city center.

  • How long is the flight from Midland to Caribbean?

    Airlines like American Airlines, United Airlines, and Southwest fly from Midland to Caribbean in about 7h 25m. The time it takes to get you to your destination can typically vary by up to 4h 40m. The distance from Midland to Caribbean is about 2432 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Midland to Caribbean one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $208. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Midland to Caribbean for a low price.

  • What are the most popular routes from Midland to Caribbean?

    The most popular flight routes from Midland to Caribbean are Midland Intl - San Juan Luis Munoz Marin Intl, Midland Intl - Oranjestad Reina Beatrix and Midland Intl - Simpson Bay Princess Juliana.

  • Can I find deals for flights from Midland to Caribbean that include hotel bookings?

    Yes. In addition to deals on Midland to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midland to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midland to Caribbean.

  • Can I find deals for business class flights from Midland to Caribbean?

    Yes. Cheapflights offers flight deals from Midland to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Midland to Caribbean?

    Currently, April is the cheapest month in which you can book a flight from Midland to Caribbean (average of $247). Flying from Midland to Caribbean in July is currently the most expensive (average of $666). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Midland to Caribbean

Discover the top 3 airlines that operate flights from Midland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$370Average$570FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$380Average$921FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$513Average$544FlexibilityNo cancel feeOn-time63%

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